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EC Tree
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
allantoin racemase, AllR,
BFW91_04965 , HpxA, HpxA enzyme,
KPN_01788 , Racemase, allantoin,
more
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Racemase, allantoin
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AllR
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BFW91_04965
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HpxA
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KPN_01788
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(S)(+)-Allantoin = (R)(-)-allantoin
(S)(+)-Allantoin = (R)(-)-allantoin
mechanism of enzymic racemization differs from that of non-enzymic racemization
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(S)(+)-Allantoin = (R)(-)-allantoin
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racemization
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(R)-allantoin
(S)-allantoin
(S)(+)-Allantoin
(R)(-)-Allantoin
(S)-allantoin
(R)-allantoin
additional information
?
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(R)-allantoin
(S)-allantoin
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r
(R)-allantoin
(S)-allantoin
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r
(R)-allantoin
(S)-allantoin
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r
(R)-allantoin
(S)-allantoin
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r
(R)-allantoin
(S)-allantoin
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r
(S)(+)-Allantoin
(R)(-)-Allantoin
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r
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(S)(+)-Allantoin
(R)(-)-Allantoin
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(S)(+)-Allantoin
(R)(-)-Allantoin
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(S)(+)-Allantoin
(R)(-)-Allantoin
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(S)-allantoin
(R)-allantoin
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r
(S)-allantoin
(R)-allantoin
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(S)-allantoin
(R)-allantoin
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r
(S)-allantoin
(R)-allantoin
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(S)-allantoin
(R)-allantoin
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r
(S)-allantoin
(R)-allantoin
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r
(S)-allantoin
(R)-allantoin
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r
(S)-allantoin
(R)-allantoin
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r
additional information
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stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
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additional information
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stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
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additional information
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Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
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additional information
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Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
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(S)-allantoin
(R)-allantoin
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r
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Hydantoin of N-carbamoyl-L-methionine
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dithiothreitol
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preincubation for 30 min at 30 C stimulates
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0.4
(R)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
1.1
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
2.3
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
0.3
(S)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
2.5
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
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43
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
57
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
238
(R)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
129
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
183
(S)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
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19
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
595
(R)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
16
(S)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
610
(S)-allantoin
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in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
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additional information
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20 - 60
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20°C: about 35% of maximal activity, 30°C: 67% of maximal activity, 60°C: about 85% of maximal activity
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brenda
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brenda
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UniProt
brenda
gene hpxA is not essential for growth on allantoin
UniProt
brenda
gene hpxA is not essential for growth on allantoin
UniProt
brenda
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UniProt
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UniProt
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physiological function
conversion of allantoin to allantoate is the second of the two ring-opening steps in purine utilization
physiological function
mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
physiological function
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mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
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25578
x * 25578, calculated
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?
x * 25578, calculated
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x * 25578, calculated
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hexamer
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trimer of dimers, X-ray crystallography
hexamer
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trimer of dimers, X-ray crystallography
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hexamer
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trimer of dimers, X-ray crystallography
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hanging drop vapor diffusion method, using 24-34% (w/v) polyethylene glycol 400 with 0.1 M sodium acetate, pH 3.7-4.1
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in cubic and orthorhombic crystal forms, at 2.10 and 2.15 A resolution, respectively
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C184S
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the mutation leads to total loss of activity
C79S
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the mutation leads to total loss of activity
C79S/C184S
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the double mutation leads to total loss of activity
C184S
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the mutation leads to total loss of activity
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C79S
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the mutation leads to total loss of activity
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C79S/C184S
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the double mutation leads to total loss of activity
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C184S
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the mutation leads to total loss of activity
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C79S
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the mutation leads to total loss of activity
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C79S/C184S
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the double mutation leads to total loss of activity
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E78D
mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
E78Q
loss of catalytic activity
E78D
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mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
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E78Q
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loss of catalytic activity
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additional information
gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
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gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
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gene insertion mutant, gene hpxA is not essential for growth on allantoin
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additional information
The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
additional information
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The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
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6.5 - 7
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up to 70°C, 15 min, stable
2445
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70
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15 min, pH 6.5-7, stable up to
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repeated freezing and thawing inactivates
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4°C, stable for several weeks
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Ni-NTA resin column chromatography, gel filtration
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expressed in Escherichia coli B834(DE3) cells
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enzyme belong to a 23-gene cluster that encodes the enzymes for utilizing purines as the sole nitrogen source
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Okumura, I.; Yamamoto, T.
Enzymic racemization of allantoin
J. Biochem.
84
891-895
1978
Cyberlindnera jadinii
brenda
Van der Drift, L.; Vogels, G.D.; van der Drift, C.
Allantoin racemase: a new enzyme from Pseudomonas species
Biochim. Biophys. Acta
391
240-248
1975
Comamonas testosteroni, Pseudomonas putida, Pseudomonas fluorescens
brenda
Pope, S.D.; Chen, L.L.; Stewart, V.
Purine utilization by Klebsiella oxytoca M5al: genes for ring-oxidizing and -opening enzymes
J. Bacteriol.
191
1006-1017
2008
Klebsiella oxytoca (B5B0K3), Klebsiella oxytoca, Klebsiella michiganensis M5al (B5B0K3), Klebsiella michiganensis M5al, Klebsiella oxytoca M5al (B5B0K3)
brenda
French, J.B.; Neau, D.B.; Ealick, S.E.
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase
J. Mol. Biol.
410
447-460
2011
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae Trevisan MGH78578, Klebsiella pneumoniae subsp. pneumoniae MGH78578
brenda
Cendron, L.; Ramazzina, I.; Puggioni, V.; Maccacaro, E.; Liuzzi, A.; Secchi, A.; Zanotti, G.; Percudani, R.
The structure and function of a microbial allantoin racemase reveal the origin and conservation of a catalytic mechanism
Biochemistry
55
6421-6432
2016
Pseudomonas fluorescens (E3SAZ9), Pseudomonas fluorescens DSM 50090 (E3SAZ9)
brenda
Bovigny, C.; Degiacomi, M.T.; Lemmin, T.; Dal Peraro, M.; Stenta, M.
Reaction mechanism and catalytic fingerprint of allantoin racemase
J. Phys. Chem. B
118
7457-7466
2014
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae ATCC 700721
brenda
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